Let's Be Friends With Our Future Selves

Our big setbacks are their bumps in the road

Who is our future self? Unfortunately, it’s usually a stranger.

“Present self screws over future self,” psychologist Tim Pychyl told Wired. That’s because we see our future self as someone totally disconnected from us, which means we don’t owe them anything.

But what if we were able to think of our present self and future self (and past self!) as the same? Would we be less caught up in momentary changes? Would we see our future as more connected to our present?

I got an answer to this recently while talking with Adam Singolda, a CEO who experienced a major setback — and saw it not as a loss, but as a natural part of the journey forward.

I want to tell you about how he thought through this, because I think it can help us all be a little better to our present selves… and our future selves.

The big thing that never happened

Adam is the founder and CEO of Taboola, the company that makes many of the content ads you see underneath news articles across the web. For example, stuff like this:

Let's Be Friends With Our Future Selves

Side note: Who in the world is thinking, Phew—had I not read this article, I would have totally picked up that normal-looking spider with my bare hand. NOOOO.


Shortly before the pandemic, Adam made big news: Taboola was merging with Outbrain, its nearest competitor, and he’d be the CEO of both companies. Then the deal fell apart, thanks to the pandemic and some other stuff.

When I saw what happened, I thought Adam must have had a hard time adjusting. Once he’d shifted into thinking of himself as the CEO of both companies, wouldn’t it be difficult returning to run just one of them?

That’s how I think, at least. If I adjust my mind to some future thing, suddenly my current thing feels small and less satisfying. It’s like applying for a job, which means thinking about the job and coming to want the job and imagining yourself in the job. Then if you don’t get the job, your current role suddenly feels like a consolation prize.

So I called Adam to see how he was adjusting after the deal fell through, and we spoke for my podcast Problem Solvers. As it turned out, he handled the setback in a totally different way than I expected.

Adam said that, yes, it was difficult to let go of the idea of this big new thing. But that was OK, because it was never going to be the only big new thing.

“You have to really believe in your journey,” he said, “and you have to really work hard for your luck.” He’s been through a million ups and downs in his career, and he’s come close to losing his company at least a few times. “I’ve seen bad stuff,” he said. “If you’re doing things for the journey, and you have people around you that make you feel invincible, then [failure is] a moment in time. It doesn’t define you.”

The deal falling through isn’t the final chapter of Adam’s company, or even his career. It was never going to be the final chapter. It is just one loss, in one moment, in a journey that will never be defined by any singular thing. In fact, Adam has already experienced another big moment: This summer, Taboola went public.

Our present self is our future self

This is why I started to think about how we exist on our timelines. The truth is, any loss for any person is just “a moment in time.” Sure, it feels giant when we’re going through it. But in the future, even the biggest setbacks become just one event from our past.

It looks pretty small there, doesn’t it?

Future self has the benefit of time. Present self has the benefit of looking towards future self. We should befriend each other. That way, we benefit no matter what time we’re in.

After all, there’s a reason I named this newsletter “Build for Tomorrow” — not “placate your feelings right now.”


What I’m reading

My friend Jai Chakrabarti wrote a beautiful new novel, A Play For The End of the World, which I’ve been looking forward to and just cracked open. The description: “A dazzling debut novel—set in early 1970's New York and rural India—the story of a turbulent, unlikely romance, a harrowing account of the lasting horrors of the Second World War, and a searing examination of one man's search for forgiveness and acceptance.”

The Washington Post loved it. Maybe you will too!


Cover Photo: Garidy Sanders, Unsplash.com